


The Mailman is Really Attractive and Dean is Smitten

by samwisewinchester



Category: Supernatural
Genre: Angst, Anxiety, Bottom Dean, Cute, Dean Winchester Feels, Dean is Bad at Feelings, Depressed Dean Winchester, Depression, Destiel - Freeform, First Time, Fluff, Fluff and Smut, Fluff without Plot, Happy Ending, I dont have a beta, Letters, Loss of Virginity, Love Letters, M/M, Mailman AU, Minor Character Death, Smut, Tooth-Rotting Fluff, Top Castiel, Vanilla, Virgin Castiel, dont worry its not bad, im actually kind of proud of this one, way too many references but I cant help it its how my mind works
Language: English
Status: Completed
Published: 2018-04-04
Updated: 2018-04-04
Packaged: 2019-04-17 23:50:51
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,722
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14200332
Author URL: https://archiveofourown.org/users/samwisewinchester/pseuds/samwisewinchester
Summary: Dean always saw checking his mail as a happy and hopeful experience; it was full of possibilities and potential, because you never knew what you were going to get. Of course, Dean never suspected that his optimistic outlook towards the US Postal Service would bring him much of anything other than the occasional surprise package or magazine. Basically, he never meant his optimism in a literal sense. But, you know, life had different ideas.When Dean first saw the new mailman, his body had such an immediate and visceral reaction, he had to excuse himself to his bedroom for a little quality time with his right hand.





	The Mailman is Really Attractive and Dean is Smitten

**Author's Note:**

> If you're looking for an update on Shopping for Love, sorry, but plotbunnies call to me!
> 
> Also, Rome wasn't built in a day, but this fic was written in one, so please don't be too harsh? And I've never really written smut before, soooooo... yeah. Oh, and disclaimer: I know NOTHING about what it's like to work for the USPS, so if I got some detail wrong, please just suspend your disbelief.
> 
> Omg, and don't judge the title, because it's literally the only thing I could think of, and at 3:30am, it was hilarious!

When Dean first saw the new mailman that Saturday afternoon, his body had such an immediate and visceral reaction, he had to excuse himself to his bedroom for a little quality time with his right hand. 

Seriously, it was insane; nothing like that had ever happened to Dean. He only figured out that he was attracted to both girls _and_ guys about a year ago, but he’d never even had that sort of response to a girl. And what’s worse? It was one of the best experiences he’s ever had jacking off. 

Like, no shit, that mailman was the hottest human Dean ever laid eyes on, and he wasn’t even Dean’s type! Dean had always gone for the petite guys, because you know, he was a dom. Well, with guys he was. He had actually started experimenting letting girls top him, and much to his own embarrassment, he actually really liked it. There was something about someone else being in control that was hot as fuck. But, just girls. He wanted nothing in his asshole, ever, thank you very much. But anyway, even though he only ever had pursued twink-types, the mailman was buff as fuck. He had looked like he was about Dean’s height, and the summer heat-induced sweat made for a uniform that clung to his body just so Dean could see rippling muscle underneath. And the shorts, no matter how silly looking for being as short as they were, let Dean see the legs of either a runner who swims in his spare time or just the legs of an actual Adonis. And his forearms! God, so strong and tanned and--Dean noticed he was developing another situation down south and forced himself to concentrate on gross things like old people making out or his brother Sam’s face. Good, good; the situation went back down. 

~***~

An uneventful week later, and Dean was back looking out his front window, shamelessly watching and waiting for the new mailman. He had no idea if he was actually going to come around again; hell, he might have just been filling in that one day for the old guy that Dean normally saw bringing the mail. 

But Dean’s curiosity was rewarded, because after about ten minutes of casual spying, he noticed the mailman walking up the sidewalk with his messenger bag over one shoulder, radiating sexual appeal. God, he was just as hot as last week. 

Oh my god, wait, he walked by the mailbox and towards the door. He was coming to the door. He probably had a package or something. But not the porno kind. Shit, what if he saw Dean last week? Dean jumped behind his couch as fast as humanly possible and tried to not breathe, because nobody was home. No one. Was. Home.

The doorbell rang, and Dean sucked his breath in and froze. Shit, the TV was on. He had completely forgotten it, and now the sexy mailman was going to know he was hiding like a kid afraid of Jehovah’s Witnesses, and he was going to judge him ughhhh. Suffice to say, Dean was fucking embarrassed. 

He waited a solid five minutes before sneaking back to the window and checking the mailman was gone before opening his front door and grabbing the package off the step. His embarrassment was forgotten quickly, because it was his Star Trek phaser from ThinkGeek! Charlie was going to be sooooo jealous, and he couldn’t fucking wait to gloat. He snapped a picture of it and shot it off to her.

Dean: _Looks like I win the gayness contest, because I can set phasers to STUN #2fab4u_

Charlie: _Oh my god, it came!!_

Charlie: _You had better bring that to work Monday so I can play with it_

Dean: _Only if you promise to not break it_

Charlie: _Btw did you see the hottie today??_

Dean: _Duh where did you think the package came from?_

Charlie: _DID YOU TALK TO HIM?!?!_

Dean: _You kidding? No way, Jose_

Charlie: _Ugh you’re no fun_

Charlie: _Wait. I have an idea! You should write him a letter and put it in your mailbox so he can read it when he brings your mail!!_

Dean: _Do you even know me? Charmando, I wouldn’t do something like that if my life depended on it_

Charlie: _You’re such a scaredy cat, Winchester_

Dean: _And proud_

 

~***~

Drunk Dean sometimes did things that Sober Dean had to pay for, especially when his best friend/arch nemesis Charlie was involved. They always went for drinks together after work on Fridays, and somehow Dean always ended up being the only one of the two of them that did stupid, drunk person stuff. He was beginning to suspect that maybe she didn’t actually even drink, just pretended to so that she could talk his more malleable alter ego into doing what she wanted him to. Like, just a random example, writing a note to the sexy mailman. 

He was going to kill her. Saturday morning met him with a skull splitting headache, and more importantly, oodles of regret. Because yes, he could vaguely remember sitting down with a pen and a piece of paper last night and writing… something. God, he couldn’t remember what the hell he had written. Maybe he had enough time to run out to the mailbox and take it out before it was too late!

Dean pulled on his sweatpants and charged out into the painfully bright midday sun. Despite his body’s many protests, he made it to the mailbox in record time, but it was for nothing, because when he opened it up, the note was gone and had been replaced by what looked like a bill and some coupons for pizza. He couldn’t really be sure, because his eyes felt like he was stabbing them full of needles. He defeatedly walked back into his house and pulled out his phone.

Dean: _Dude. What happened last night. Tell me or I’m going to send your girlfriend your prom photos_

He waited for a response while chewed discontentedly on a piece of cold bacon from the fridge and sipping a glass of water. He didn’t have to wait for long though, and he soon heard the telltale R2-D2 beep that was Charlie’s text alert noise. 

Charlie: _You were so plastered, my man. It was wild._

Charlie: _I take it you only just woke up and didn’t have time to get the letter out of the box?_

Dean: _Shit, so that really happened? Dear god, tell me I didn’t write anything too embarrassing?_

Charlie: _You politely told him you wanted to suck his dick_

Dean: _I’ve got the picture ready to send!_

Charlie: _Ugh, fine. No, all you said was that you thought he looked nice and were wondering what happened to the old guy who used to bring your mail. Tbh it was pretty cute. I love drunk you_

Dean sighed in relief. It was still as embarrassing as balls, but maybe the guy will think Dean has a kid or something and they wrote it. He can only hope at this point. 

~***~

When Dean got home from work Monday evening and opened up the mailbox, his hopes that the mailman would just ignore the letter were proven to be in vain. 

Sitting there in the box, on top of a classic car magazine he subscribed to, was a small blue envelope with no stamp and just his first name in rather lovely script in the middle. He ripped it open before he even got inside, because holy fuck, there’s no one who would drive by his house just to put a letter in my mail other than Mr. Sexypants. It read:

Dear Dean,  
I’m guessing by your handwriting and subject matter that you’re either a child or a drunk man. If it’s the former, please tell your parents that I am not a pedophile. Please. If you’re an adult and just have terrible handwriting, I’m sorry for touching on a sore subject.  
Anyway, Cain, your previous mail carrier, was only working your route temporarily. He actually is one of the higher-ups for the USPS and was delivering mail as a sort of extended vacation from management. Odd, I know.  
I appreciate that you think I look nice, and if you’re the adult male who lives at this address, I think you do too. If you’re a child, I’m sure you look nice, but in a non-pedophilic way.  
Yours,  
Castiel 

Oh my god, Dean was in love. Haha, just kidding. He’s not in love; what are you talking about? Totally not in love. Nope, not at all. He lunged inside, pulled off his jacket and sunglasses, and began furiously debating whether or not to tell Charlie about this. On the one hand, she’s his only real friend besides his younger brother, who is constantly busy with lawyer-things. But on the other hand, she would totally gloat about this for the rest of her life. But fuck it, he needs to talk to someone about this, because he never has romance in his life! 

Dean: _Omg you’ll never believe what happened\\\_

__

Charlie: _Ooh! What??!_

__

Dean: _Mr. Double Stuffed Hotness is named Castiel, and I might want to marry him_

__

Charlie: _HE WROTE BACK?!?! It’s fate, my young grasshopper_

__

Dean: _I’m gonna send you a pic of the letter he wrote back so you can help me figure out what to write back_

__

Charlie: _You had better let me be your best man!! AND let me officiate!!! I’m already planning my speech_

__

Dean: _Don’t get ahead of yourself… but I’m actually kind of psyched rn_

And so the planning began. Eventually, they decided on a note that read the following:

Dear Castiel,  
As you deduced, I was drunk. Don’t worry, I’ll tell my parents you aren’t a pedophile anyway, just in case. Of course, they’re both in their 60s and will probably also assume I’m drunk, but better safe than sorry.  
Thank you for saying I look nice, though I can’t imagine when you’ve seen me. I’m normally at work when you bring the mail (around 1:30pm, right?), so have you seen me on a Saturday? Okay, you don’t need to answer, just in case you’re actually a stalker or something. It’s never good to confront the bad guy in horror movies, and I’ve learned my lesson.  
Hey, is your name really Castiel, or is that a pseudonym? I googled it, and it’s the name of the Angel of Thursday? What’s so special about Thursdays?  
Live long and prosper,  
Dean

~***~

Dear Dean,  
I’m very glad I won’t be going to jail for calling a child attractive. You can probably hear my sigh of relief from there.  
I can neither confirm nor deny when/where I have seen you. Also, are you calling me the antagonist of a horror film? If so, please enlighten me on which one, because I’m rather a fan of being scared shitless, and I’m sure seeing myself as the murderer will make an horror viewing experience even more terrifying.  
And yes, my name is really Castiel. Let’s just say my parents were hippies. Many people call me Cas, though, and my siblings call me Cassie. I don’t like my siblings very much.  
What about you? Why are you named Dean? Did your parents hope you would create a list of exceptional people? Or perhaps they wanted you to grown up to resemble Dean Martin?  
I’m sorry, I don’t know where all that rude sass came from; it’s been a long day.  
Khaaaaaaaaaaaaaaan,  
Cas

~***~

Mr. Spock,  
I had a girlfriend named Cassie once! Sort that information away for a future test, I suppose. How many siblings do you have? I one brother, and he can be such a bitch sometimes, so I definitely get where you’re coming from.  
As it happens, I’m named after my grandmother, Deanna. And I swear to god, if you make fun of me for that, I will, um, do something… I don’t know exactly what yet, but I’ll figure it out, and it’ll be awful, I promise!  
So, is it really that hard being a mailman? (You said it had been a rough day.) I’m a mechanic, by the way. If you ever need to know anything about cars, just hit me up, and I’ll be happy to help. For a price… Ha, just kidding. Maybe…  
Dammit Cas, I’m a mechanic, not a doctor!  
Dean

~***~

Bones,  
I find it slightly perturbing that my nickname is also the name of your ex. But I always ace tests, so I guess I’m glad to know it anyway.  
I have 5 siblings. I know. Hippies don’t believe in birth control, I guess. But yes, family of 8, from Michael the oldest, down to Sam the youngest. Since I’m on the subject, I suppose I might as well list off all my siblings. There’s Mike, Gabe, Luce, me, Anna, and Sam, ranging in ages from 37 to 21. Oh, I’m the ripe old age of 29, by the way. Not that that matters. Jesus, this entire letter is me talking about my family, sorry.  
And no, it’s not hard being a mailman, but it is hard having to take your beloved cat to the veterinarian because they’re refusing to eat, not having bowel movements, and rolling around on the floor, meowing in pain. The poor guy had a blockage and almost died. It was a tough day.  
I might just take you up on your offer to help explain things about cars, because I am completely clueless about them. I drive an old clunker that eats gas money like nobody’s business, and I really need to get a new car as soon as possible.  
Have you been at the Romulan ale again??  
Cas

 

~***~

Castiel,  
I know I signed my last note with a Bones reference, but make no mistake, I am 100% Kirk, and I would appreciate it if you referred to me as such. Thank you for not forcing me to pursue legal action.  
Dude, my younger brother is named Sam! Well, technically he’s named Samuel, after our grandfather, but still. Weird. And I’m 32, so that’s cool I guess.  
I’m sorry to hear about your cat; that sounds pretty awful. I’ve never really had pets, and I’m actually allergic to cats, but I remember when Sammy’s dog was hit by a car and how distraught he was. I’m guessing your cat is all right now, though? If so, I’m glad. If not, sorry for rubbing salt in the wound.  
Dude, do not drive that car. Like, stop it now. Please, for the sake of car lovers everywhere. Take it down to Singer’s Auto Salvage Yard; Bobby is a friend of mine, and if you tell him I sent you, he’ll give you a good price for it, and then you can use that money to buy something that’s not a piece of shit.  
*funny Star Trek reference here*  
Captain James Tiberius Kirk

~***~

 

Jim,  
Can you sense me rolling my eyes? Because there’s some serious ocular oscillation going on right now in reference to your threats.  
And I shortened my Sam’s name, too. His full name is Samandriel. Hippies, am I right?  
Yes, my cat is fine, thank Talos. He is my best friend, and I don’t think I would be able to function properly if something happened to him. He’s a black shorthair named Toothless, by the way. Yes, I’m a basic bitch. Bite me.  
I’ll try and take your advice about the car. I think my car is actually the automobile form of Sauron’s ring of power, because every time I’ve tried to get rid of it, it talks me into keeping it. I know in my heart that it needs to be torn apart for scraps, that it is taking advantage of me and should be destroyed before it does something terrible, but it’s mine. My own. My...precious…  
Oh, my biggest problem is that if I sell her, I don’t know anything about buying cars, so I’m afraid someone will take advantage of my naivete and sell me an equally shitty car for a ridiculous price. Any suggestions?  
*I can do this too*  
Spock Spock Spock-ity Spock

 

~***~

Spockity,  
God, I wish my parents had been hippies. Instead they were hippos. Yep, I was adopted by a pair of hippopotami at the age of four. Don’t believe me? Ask the Topeka Zoo, and they’ll corroborate my story. (Please don’t actually do that; they might remember me from when I was a teenager and broke in there to try and pet the giraffes.)  
And I will never judge anyone for loving How To Train Your Dragon, because that movie was legendary. Toothless is the cutest dragon probably ever, and Hiccup is such a dreamboat.  
Um, we definitely need to get rid of that car. Do not take me for some conjurer of cheap tricks! I’m trying to help you. And speaking of helping you, if you find a car and want to know just how swindled you’re going to be, just send me the information, and I can let you know if you should buy it or not!  
So… what kind of music do you like? I’m a big classic rock fan, and if you aren’t I will become determined to change that about you.  
Can we up switch references? Maybe Princess Bride or something?  
Princess Buttercup

~***~

Buttercup,  
I find your story inconceivable. But did you truly grow up in Kansas? Personally, I grew up in the wilds of Washington; Seattle, actually.  
And good; I would be very upset with you if you didn’t love Toothless and Hiccup, though I must say Hiccup is not exactly my type. I like my men a little older than he (recall that I’m not a pedophile), and I think any man I may date should definitely be my size or larger, or else I might kill them accidentally in bed. Huh, I guess we haven’t really talked about sexuality ever, so sorry if that made you uncomfortable.  
I would greatly appreciate it if you would actually send me your phone number or email or something, so I could send you the information on a car I’m seriously considering buying. If you’d rather not hand out such personal information, I completely understand though.  
I confess I haven’t listened to much classic rock. I mostly listen to classical music, though I’ve been delving into the genre of lofi hiphop, and I actually really enjoy it.  
As you wish,  
Vizzini

 

~***~

Vizzini,  
You keep using that word; I do not think it means what you think it means…  
Yes, I grew up in Kansas, a little town called Lawrence to be precise. And the bit about breaking into the zoo was real too, so please don’t report me.  
And honestly, I’m kind of in a weird experimental stage with my sexuality right now. I know, that’s supposed to happen during college, but maybe I’m just not a normal guy, all right? Anyway, I think I’ve officially decided I’m bisexual, but who knows? Romance is tiring, but sex is fun, and I don’t really mind who the hole belongs to. Jesus, that sounded awful and disgusting; sorry. I’m not even really like that any more. I haven’t had a hookup for like three months, which has got to be some kind of record. Sorry, this I should stop writing while I have the chance.  
Totally send me the deets about the car, man. My number is 1-866-907-3235  
Dude, I’m going to indoctrinate you. You fucking need to listen to classic rock; it’s the stuff of gods. Maybe I’ll make you a mixtape or something so you can listen to all the best songs. Weird question: do you have a tape player? I’m kind of old fashioned, so yeah, I’m going to make you a cassette tape with my favorite Zepp tracks on it.  
Mahwage, dah bwessed awangment,  
The Dread Pirate Roberts

~***~

For some reason, it was taking Cas a long time to get back to Dean. They had kind of worked out an unspoken schedule by this point; one of them put a letter in the box Monday, the other responded by Wednesday, and then the first sent back a response the Friday of the same week. Basically three letter a week for the past month or so. No, that’s not weird or creepy for two adult men to do at all. 

Dean had dropped off that last letter on a Monday, but no reply came on Wednesday. He tried to not let it bother him, thinking Cas was probably busy or something. But then there wasn’t a reply Thursday or Friday either, and he started to get a little miffed. The least Cas could have done was to text him now that he had his number, but noooo. Unfortunately, Dean had to be out of town that Saturday, so no confrontation could happen over the 1:30 mail delivery. 

The next Saturday rolled around with no word from Cas again, and Dean was starting to get legitimately worried. He would have understood if the guy took some time off maybe for being sick or something, but two weeks? Nobody takes two weeks off, especially without telling their… friend? Suddenly, Dean’s ridiculous number of insecurities started blaring at him. What if he and Cas weren’t friends? What if he didn’t actually mean anything to Cas at all? He probably was just another drain on Cas’ time, and Cas had finally decided he’d had enough and didn’t want to talk to Dean anymore. Hell, he might have requested a different route because Dean was harassing him. Shit, of course all this was too good to be true. Dean never made friends; Charlie was the only acception to that painful trend, and he had no idea why she still hung out with him. 

Dean knew those thoughts too well; he knew his own self-loathing always came around and wouldn’t leave until he started thinking about other things. So, he thought about Cas. It was almost 1:30, two weeks since he’d heard from him last, and he decided to camp out at the mailbox and wait for whoever came. He had to know if Cas was all right, at least. The guy was his friend, even if maybe Cas didn’t see him as one. 

He didn’t have long to wait before seeing his old mailman (Cain, was it?) peddling a sleek bicycle down the sidewalk with a messenger bag slung over his shoulder. 

“Um, hey, sorry to bother you. Cain, is it?” Dean fidgeted, feeling awkward as fuck.

“Yes, that’s me. Can I help you with something?” Huh, okay, Cain seemed like a pretty chill guy. Maybe Dean could actually avoid a panic attack from doing something this wild. 

“Uh, yeah. Do you know Castiel? He brought mail on this route for a while? I just haven’t seen him in a while, and I was worried that something happened.” Dean was talking too fast, but he couldn’t help it, okay?

“I know Castiel, and I know he took off a few weeks. Don’t know why though; maybe a vacation or something. I wouldn’t worry about it though, if I were you.”

Oh Dean was gonna worry about it, no doubt about that. Because wow, he was glad Cas was all right and not dead somewhere, but Jesus, what kind of douchebag friend goes on an extended vacation without so much as a goodbye?? So yeah, Dean was going to worry about what he did wrong and why he never could keep friends, and why he was such a fucked up excuse for a human being. Awesome.

~***~

Dean was depressed. Charlie tried cheering him up but to no avail. He was just depressed. He actually took the day off on Monday, because he was such a fucking sissy who couldn’t deal with anything. God, no wonder Cas didn’t care about him. No one should care about him; he was so pathetic. 

The doorbell rang. Dean lifted his head from the pillow it had been buried in for the entire first half of the day and decided he probably ought to answer the door, seeing as there was a 98% chance it was Charlie with pie and beer and a chick flick to make him feel better. God, she was too good for him; he didn’t deserve such a good friend. 

He pulled the door open and was greeted by the invisible man; wait no, there was a package and a pile of mail on the front step. He sighed and picked it all up, then promptly dropped it all on the floor, shut the door, and collapsed on the couch. He didn’t feel like looking at the mail. He didn’t feel like doing anything except for sleeping. Ugh. 

But maybe that package would cheer him up. He rolled his eyes at the tiny optimistic voice in his head and then rolled right off the couch and crawled to the pile of mail. He grabbed package without so much as glancing over the letters, probably all bills, and violently tore it open. Ooh, it was those custom leather-bound journals he ordered off Etsy. One was embroidered with his Hogwarts House logo (Hufflepuff and proud!) and the other matched it but had Charlie’s House (Ravenclaw, more like Raven...dumb! Good one). One of the few things he was ashamed of about being a sissy was doing things like buying matching things for himself and his best friend, or having sleepovers with his best friend, or planning his future wedding with his best friend. ANYway. 

Okay, cool, the opening the package plan had worked! Dean was feeling better already. But then he saw it. Underneath the topmost bill was a little blue envelope. Dean’s hand had never moved so fast (yes, never).

Sure enough, it was from Cas. But unlike all the other letters Dean had gotten from him, this one was stamped and had both mailing and return addresses on it. Without stopping to think about what the fuck that could possibly mean, Dean ripped open the letter and read:

Dear Dean,  
I am so sorry I haven’t written you in so long. To put it succinctly, my father had a heart attack, and I had to go to to Washington to be with him. The past two weeks have been about family and rekindling our relationships with each other. My father passed away two nights ago, and the funeral was yesterday. I know we never really talk about serious things, but I hope you won’t mind if I tell you this.  
Honestly, as heartbroken as I am to see my father pass, I’m grateful that it has brought my family back together. All of us were there with him at the end, all of us were gathered around his bedside as he breathed his last. And he went peacefully, so I’m also grateful for that. I’ll be staying up here for another few days before flying back, and then I’ll be back to work as normal. I put my address that I’m staying at while I’m in Seattle as the return address, but I’ll add my home address too at the bottom of the page; it only feels fair that since I know where you live, you should know where I do too.  
Again, I’m sorry if I made you worry at all. I know you might not see me the same way, but you’ve actually become one of my closest friends over the past month. What that says about my personal life? That I’m very awkward and antisocial, that’s what it says.  
I hope to talk to you soon,  
Castiel

Thank the fucking lord. Dean let go of a breath he hadn’t realized he’d been holding and grabbed his phone.

Dean: _Cas is okay!! His dad died but he’ll be back soon_

Charlie: _Wait, his dad died, but he’ll be back soon? Who is he, god? I mean, Jesus. Whatever, I’m not required to make good religious jokes_

Dean: _Haha, very funny_

Charlie: _But yay!! I’m so glad for you!! Maybe now you’ll stop sulking like a little lost puppy_

Dean: _I make no promises_

~***~

As promised, Cas was back by the end of the week, and Dean couldn’t stop grinning when he looked out his window Saturday to see Cas walking up to his mailbox.

He pulled the door open and ran out, unprecedented behavior from the man afraid to make eye contact with girl scouts selling cookies outside the front of the grocery store. 

“Cas! It’s good to see you, man!” He went in for a hug, but then it got a little too real, so it ended up being one of those awkward side-hugs that no one really likes but everyone has to deal with.

Cas smiled back widely, and Dean got a little lost in his eyes. Wow, he’d never actually seen Cas up close, and now that he did, he could tell that Cas was actually the most attractive man alive. His ocean blue eyes drew Dean in, and he found himself completely phasing out to the point that Cas had to repeat a question three times before he could respond.

“Sorry, um, what was that?” Was the response. Classic.

“I asked if you were all right; you look a little phased.” No shit, Sherlock.

“Uh yeah, I’m fine. Just a little tired.”

“I was a little worried I’d scared you off with my last letter, seeing as how you didn’t write back.” Shit, Dean had forgotten to.

“Fuck, I totally forgot that I had your address. I guess I’m not used to actually properly sending letters, not just putting them in the mailbox.” They shared a quiet laugh before Dean went on, somberly. “I’m really sorry about your dad. My mom passed a few years back, and I know how painful it is.” 

Cas smiles sadly. “Yeah, it was rough, but like I said in the letter, it really brought my family together, and I’m sure dad would have been happy to see the impact he had on us.” He paused, and Dean could there was something more rolling around in his mind, so he decided to stay silent and let Cas finish his thought. “It’s funny, he was such an absent father when we were growing up. I know he was different when he and my mom were first married; I think he was a carpenter or something, and he was always at home with Mike and Luce when they were little. But then his business took off, and by the time I was in diapers, he was hardly ever around. Business trips, late nights working, early morning meetings, it never ended. It kind of tore our family apart, bit by bit. First, Gabe ran away when he was 16. He didn’t get in touch with any of us for almost a whole year. Later, he told me he just couldn’t stand to see all the arguing and pain in our family. Then it was Luce, angrily storming off to college and refusing to answer our calls or emails. He loved all of us, his siblings so much, and I think watching dad’s absence affect us younger kids really took a toll on him.”

Suddenly, Cas’ eyes flashed up, and his cheeks grew pink. “Oh my god, I’m so sorry, I’ve just been standing here, telling you my life’s story. And fuck, I’m on the clock; I really need to run.”

Before Cas could move, Dean grabbed his wrist. “Wait, can you give me your phone number? I put mine in my last letter to you, but I’m guessing you didn’t get that.”

They exchanged numbers as quickly as possible, and Cas ran off towards the next house on his route. Dean grinned as he watched his run away and immediately send him a trial-run text.

Dean: _If you gave me a fake number, I’m going to go to your house and shave your cat_

Off in the distance (only about 200 feet, to be perfectly honest), Cas stopped and looked down at his phone, and Dean could not hold back a huge laugh. 

Castiel: _Toothless would kill your sorry ass_

~***~

Regina George,  
Oh my god, you’re so fetch.  
Sorry Cas, I don’t know why, but I really felt like I had to change our theme to Mean Girls. Sue me. (Also, you better have fucking watched Mean Girls, or there will be hell to pay.)  
So, my friend Charlie talked me into this, but I guess I kind of agreed with her that I ought to do it. And you can totally say no thanks, not interested, and it’ll be completely fine! But, I was wondering if maybe you’d be interesting in going on a date with me sometime…?  
Wow, I am a child. Well, a teenage girl, to be precise. Oh shit, and you keep telling me you’re not a pedophile, so you’re definitely not going to want to go out with me now that you know my true identity. Well this is a fine mess I’ve gotten myself into.  
Have you sold that car yet? You should really get on that.  
Yours forever,  
Amy Poehler 

~***~

Mother,  
Of course I’ve seen Mean Girls, I’m not that out of the proverbial loop.  
And would you please thank your friend Charlie for me? I’ll admit, I’ve wanted to go on a date with you for a quite a while now, but ye ole’ social ineptitude wouldn’t let me ask. Maybe text me when you get this, and we can work out a time/place? Saturday nights are usually best for me, considering I’m always off Sundays.  
Please Dean, if you’re a teenage girl, then I am too, and then it’s not pedophilia.  
And no, I haven’t sold it yet, because I haven’t decided on a new one to buy yet, because in case you hadn’t noticed, my life has been a little hectic lately. I’ll try and text you the details on the car I’m looking at soon, though.  
Fours yorever,  
Reginers 

~***~

Saturday night is there before Dean can get his shit together. He had frantically texted Charlie minutes after making the date with Cas asking her what he should wear and how he should act and whether he should just run away and never come back. You know, normal stuff.

In the end, he and Cas had decided on meeting an a small burger place near Cas’ place, so Dean knew he shouldn’t wear something too fancy. But he didn’t want to wear just his every minute of every day bluejeans, t-shirt, and flannel combo. So, with some sagely advice from Charlie, he’s decided on his most flattering pair of grey jeans and a button down maroon shirt, freshly ironed. Honestly, not half bad, even by his self-degrading standards. He toyed with the idea of a grey tie with the top two buttons of his collar undone, and decided it was too snazzy for him to refuse. 

A 15-minute drive later, he was walking into the restaurant and looking around for Cas. And boy, did he find him. Cas was wearing a tight pair of black jeans, an Egyptian blue button down, and a black waistcoat, and holy fuck, Dean was having another southward situation just at the sight. He repeated the words ‘puss, flesh, old-people skin,’ in his head for half a minute until everything was hunky dory again, then made his way to the bar where Cas was standing. 

“You look great, Cas.” Dean grinned when he saw Cas blatantly checking his ass. The good old grey jeans never fail. 

“As do you, Dean,” Cas responded, his pupils mildly larger than probably normal. 

They made their way over to a small corner booth and waived down a waitress. Adorably enough, they both ordered the same bacon cheeseburger, and in the time it took for their food to arrive, they discussed possible future heart health and how they were both going to die eventually, so it might as well be from eating delicious food.

“Dude, if bacon’s what gets me, I win,” Dean remarked right before taking a huge bite into his burger. 

Cas harrumphed in agreement, then moaned around the first bite of his own burger. 

Uh oh. Turned out, visual Cas is nothing compared to audible Cas in terms of making Dean’s nether regions all kinds of interested. To put it simply, Dean was sitting at a booth, on a first date, a burger in his mouth, almost completely hard. Awesome. 

“Dean, are you okay?” Shit, Cas apparently noticed the panicked look on Dean’s face, and Dean’s face burned red. 

“Um, yeah, I’m fine. I, um, just kinda have a little… situation. Downstairs. God this is so embarrassing; I’m soooooo, so sorry. Please don’t hate me.”

Cas was quiet for a second, then burst out with infectious laughter, and Dean couldn’t help but join in. “Oh my god, that’s hilarious. Was it become of the groan I just made or…?”

Dean ran a hand through his hair before responding, “Um, yeah. Fuck. Look, I haven’t gotten laid in like six months, so cut me a little slack. And honestly, I’m really sorry. I wanted this to be a really special first date, but I feel like I kind of ruined it.” Like Dean ruined everything. 

“Oh, no no no! Really, I understand much better than you’d think,” Cas assuaged his fear and sorrow with a comforting pat on the back on the hand and an amused grin. “It’s honestly fine. Now, do you need to go to take a trip to the bathroom, or are you all right now?”

Dean informed Cas that apparently humiliation was not one of his kinks, and the situation had resolved itself, and they were able to go on with their dinner like it had never happened. 

But you know, it _did_ happen, and Dean _hadn’t_ had sex in months, and Cas _was_ the hottest date Dean had ever had. SO yeah. Things happen. 

~***~

After an amazing evening of burgers, pie, beer, and literal hours of conversation, they decided it was definitely time for them to part ways. Cas had walked to the restaurant, so Dean offered to drop him off on his way home, and Cas gratefully accepted. 

The car ride was normal, if slightly tense. They were both slightly buzzed and totally attracted to each other, after all. But it was chill. 

Dean pulled up to Cas’ home, a cozy-looking apartment complex, and parked his car in one of the visitor spots. They both climbed out and walked together up to Cas’ door. 

“So, I had an awesome time tonight,” Dean half-mumbled, really trying his best to appear like he wasn’t desperate to go out with Cas again as soon as possible. “You think you might want to do this again sometime? I mean, really, I totally get it if like I’m not your type or you’re just not into me or you think I’m too--”

Cas slammed their faces (particularly their lips) together, effectively cutting off Dean’s self-abusive train of thought and filling his mind with only the pure bliss of Cas’ warm mouth on his, their tongues fighting for dominance. Cas’ mouth tasted amazing, like apple pie and happiness. Dean hungrily chased the flavour, and he couldn’t get enough. They broke for air for just a minute before Cas wheeled Dean around and up against his apartment door, weaving one hand into his hair and grabbing Dean’s own hand with the other, pinning it up against the door above his head. 

Dean had never felt less in control, and it was amazing. He could feel the strength in Cas’ body shoved up against his own. He felt vulnerable, but for once in his life, he was okay with that vulnerability.  
Cas moved his mouth down from Dean’s mouth to his neck, peppering the skin with hot, wet kisses. He settled on one spot, the meaty place between Dean’s neck and right shoulder and assaulted it with licks, kisses, nibbles, and sucks. He was driving Dean crazy, and Dean honestly couldn’t stop himself from moaning out, “Uhhhh, Cas…” 

Maybe it was something about how he broke the silence, but Cas suddenly stilled and looked up at Dean, alarm filling his eyes. “Oh my god, Dean, I’m sorry. I’ve never done this before; I don’t know what came over me.” He stepped back from Dean and rubbed his hands over his face. 

“What? Why’d you stop?” Dean replied, feeling suddenly abandoned. 

Cas locked eyes with Dean and said very seriously, “I have no idea what I’m doing, Dean. I’ve never had sex; hell, I’ve never been in a relationship that lasted longer than a week. And you’re this amazing, attractive man who has had so much sex and knows all about it, and I’m just going to embarrass myself and it’ll be terrible and--”

This time, Dean satisfies the cliche, cutting off Cas’ river of doubts with a kiss into which he poured all the words he wanted to say but didn’t know how: that Cas made him feel safe and comfortable and like he could be himself and still feel appreciated and cared for and special and important. 

Cas seemed to get the message, and he quickly took control once again, holding Dean tight in his arms and kissing him with more passion than is in an entire episode of Casa Erotica. 

Dean had been hard for a while now, and as Cas clung to him, he could feel that Cas was in about the same spot as he was. But shit, if Cas was a virgin, that would put a lot of weight on Dean’s shoulders, right? He wanted to make it perfect for Cas, because that’s what Cas deserved. 

But apparently, Cas had a completely different idea. He pulled away from Dean, and with his pupils completely blown wide and dark, moved his mouth to Dean’s ear and whispered, “I’m going to make you feel so good.” 

Huh, well, Dean realized at that moment he was completely, 100%, no doubt about it, a bottom. And apparently, Cas’ self-confidence boosted itself threefold when he was horny, so yeah. That was pretty sweet.

Cas fumbled with his apartment keys and opened the front door before pushing Dean inside and slamming the door behind them. He kiss-walked (that thing where people are joined at the mouth but still manage to move around, that’s honestly kind of impressive if you think about it) Dean to what Dean assumed could only be his bedroom and shoved him onto the bed before climbing on top of waist and resuming kissing him like a man dying of dehydration and Dean’s mouth was a fucking water fountain. 

Without breaking their lip lock, Cas scrambled to get Dean’s tie off, and Dean did his best to help with the clothing removal process, but his efforts were mostly futile. 

_Finally,_ after a pathetically long and unromantic struggle, they were both naked, and Dean was basically drooling at the sight of Cas’ dick. Like, holy hell, it’s not like Dean himself was small, but Jesus, he was embarrassed of his own length in the presence of Cas’ massiveness. 

Cas grinned with a hungry look in his eye as he took Dean in, and Dean felt suddenly self conscious as Cas scanned him so carefully. 

Cas noticed the change in Dean’s demeanor and guessed the source quickly. “Dean, you are so beautiful,” his husky voice reassured before leaning in and capturing Dean’s lips once again, this time with a contrastingly gentle and loving kiss, and for once in his life, Dean let himself actually believe that about himself. 

The kiss soon got more heated, and Cas’ hands began exploring Dean’s body, starting in his hair, traveling down his chest, over his hips, and down his thighs. Dean moaned and realized that, much to his embarrassment, he was actually close. 

Fortunately, Cas seemed to sense he should advance things, and he trailed his hands back up to Dean’s throbbing cock. Dean let out a punched groan at the first touch to his hot member, squeezed his eyes shut tight, and clenched his fists behind Cas’ back. “So good, Cas…” 

Cas’ hand left his cock for a minute, and Dean heard the telltale sounds of someone spitting before the hand returned, slick and tight. Just a couple tugs and Dean was coming with a shout. “Oh, Cas, oh fuck, Cas!” 

He had never come so quickly in his entire life, but Dean couldn’t even find it in himself to be ashamed, especially as he heard Cas grunting as he followed directly behind him. 

“Cas, that was…”

A sudden worried look fell over Cas’ face. “Was it bad? I’m sorry, I know we both came really fast.”

Dean laughed and tried his best kiss the pouting look off of Cas. “No, it was amazing, Cas. Jesus, that was the most vanilla shit I’ve ever done, but it was perfect.” Dean sighed and steeled himself before continuing. “And actually, I think the reason it was perfect was because, well, it was with you, Cas.”

~***~

“Honeybee, I’m home!” Dean stripped off his big winter coat and hung it on the hook by the front door.

“I’m in the kitchen, Dean!” Dean stalked through the house and up behind his husband, snaking his arms around the other man’s broad chest and leaning over his shoulder to give him a peck on the cheek.

“How was work today?” Dean asked, glancing around the kitchen and noticing with a grin what looked suspiciously like the mess left after someone has baked an apple pie. 

“Work was lovely, thank you. Of course, that was mostly because of the letter I got from my favorite stop on my favorite route.” Cas grinned and spun around to give Dean a proper kiss. 

“I’m your favorite?!” Dean grinned and pulled back before Cas could kiss him

Cas rolled his eyes, “No, I’m talking about our neighbor, Mrs. Tran.” 

“I love you too, babe.” Dean finally let himself be pulled into his husband’s eager arms and smiled into the kiss. Okay, maybe life's ideas were kind of awesome.

**Author's Note:**

> Did you like it??! I thought it was pretty cute, if I'm being honest... Anyway, please leave a comment and tell me what you think! I promise I'll get a new chapter of Shopping for Love out as soon as I can!!


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